N-(3,4-dichlorophenyl)piperidine-2,6-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: N-(3,4-dichlorophenyl)piperidine-2,6-dione
• 英文别名: 1-(3,4-Dichlorophenyl)piperidine-2,6-dione
• 化学式: C₁₁H₉Cl₂NO₂
• mdl: MFCD16331331
• 分子量: 258.104
• InChiKey: YSDAOHGGWJMDBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  copper(l) cyanide 、 N-(3,4-dichlorophenyl)piperidine-2,6-dione 以 N-甲基吡咯烷酮 为溶剂， 以9%的产率得到N-(3,4-dicyanophenyl)piperidine-2,6-dione
  参考文献：
  名称：

  Efficient diborane-mediated synthesis of phthalocyanines carrying amino groups near the macrocycle

  摘要：

  N-(3,4-dicyanophenyl)piperidine-2,6-dione (2) and 4-phthalimidophthalonitrile (3) were synthesized in 24% and 74% yield respectively, using 4-aminophthalonitrile as the starting material. Treatment of 2 and 3 with zinc acetate in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene gave respectively phthalocyanines 4 and 5, whose reduction with diborane afforded dyes 6 and 7. Quatemization of 6 and 7 with iodomethane gave cationic zinc(II) phthalocyanines 8 and 9 respectively. A bathochromic shift was observed in the absorption spectra when amino and ammonium groups were present near the macrocycle in comparison with those dyes carrying alkylamino and quaternary alkyl ammonium salts as peripheral substituents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.07.089
• 作为产物：
  描述：

  3,4-二氯苯胺 在 溶剂黄146 、 乙酰氯 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成 N-(3,4-dichlorophenyl)piperidine-2,6-dione
  参考文献：
  名称：

  Stiz; Souza; Golin, Pharmazie, 2000, vol. 55, # 12, p. 942 - 944

  摘要：

  DOI：

文献信息

• A Novel Synthesis of <i>N</i>-Arylamides from Nitroarenes via Reductive N-Acylation with Red Phosphorus and Iodine
  作者：Zhenyuan Xu、Xiaohua Du、Mei Zheng、Sheng Chen

  DOI：10.1055/s-2006-947334

  日期：2006.8

  A series of N-arylamides and imides were synthesized via reductive N-acylation of nitroarenes with red phosphorus and carboxylic acids, catalyzed by iodine or iodides; an I - /I 0 redox cycle was proposed to promote the reaction.

  在碘或碘化物的催化下，通过硝基芳烃与红磷和羧酸的还原性N-酰化反应合成了一系列N-芳基酰胺和酰亚胺；提出了I - /I 0 氧化还原循环来促进反应。
• Stiz; Souza; Golin, Pharmazie, 2000, vol. 55, # 12, p. 942 - 944
  作者：Stiz、Souza、Golin、Neto、Correa、Nunes、Yunes、Cechinel-Filho

  DOI：——

  日期：——
• Efficient diborane-mediated synthesis of phthalocyanines carrying amino groups near the macrocycle
  作者：Gabriela A. Gauna、Diego Cobice、Josefina Awruch

  DOI：10.1016/j.poly.2012.07.089

  日期：2012.10

  N-(3,4-dicyanophenyl)piperidine-2,6-dione (2) and 4-phthalimidophthalonitrile (3) were synthesized in 24% and 74% yield respectively, using 4-aminophthalonitrile as the starting material. Treatment of 2 and 3 with zinc acetate in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene gave respectively phthalocyanines 4 and 5, whose reduction with diborane afforded dyes 6 and 7. Quatemization of 6 and 7 with iodomethane gave cationic zinc(II) phthalocyanines 8 and 9 respectively. A bathochromic shift was observed in the absorption spectra when amino and ammonium groups were present near the macrocycle in comparison with those dyes carrying alkylamino and quaternary alkyl ammonium salts as peripheral substituents. (C) 2012 Elsevier Ltd. All rights reserved.